


A First Time for Everything

by KillerOfHope



Category: Supernatural
Genre: Anal Fingering, Begging, Bottom Dean, Embarrassed Dean, First Time, M/M, Shyness, Top Sam
Language: English
Status: Completed
Published: 2016-07-03
Updated: 2016-07-03
Packaged: 2018-07-19 20:27:45
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,033
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7376218
Author URL: https://archiveofourown.org/users/KillerOfHope/pseuds/KillerOfHope
Summary: <blockquote class="userstuff">
              <p>Bend over with his face into the pillow he couldn't see what Sam was doing but sure as well it felt good.</p>
            </blockquote>





	A First Time for Everything

**Author's Note:**

> Written for the SPN Kink Bingo. Square Filled: Winchest.

Dean's chest was heaving when two hands pulled his ass cheeks apart. Bend over with his face into the pillow he couldn't see what Sam was doing but sure as well it felt good. Actually it felt amazing. His cock had received a lot of attention just until now and Dean 'd have been completely happy hadn't Sam pulled away at the last second. When a finger slick with lube pushed past his entrance Dean made a punched out little noise. Desperately he grabbed the fabric beneath him as the finger was joined by another and they began to fuck him. Slowly. 

They went in and out. In and out. Over and over again. 

"Sam," Dean breathed. His hands trembled, just as his thighs that held his ass in the air but he didn't dare to look. "Please, I ..." 

"Shh, it's alright, Dean." His little brother rubbed Dean's lower back and picked up the pace. "Soon." 

His breath hitched as a second finger joined the first. Dean buried his face into the pillow. He didn't dare to look back and watch what Sam was doing to him, using his fingers to open him for his little brother's cock. Oh god, his little brother would fuck him. Right now it was just two fingers pumping into his ass but soon there would be more. 

"I'll use three now, Dean," Sam warned and grabbed his brother's hip as he added another finger. Of course he lubed them first and Dean's hole was glistening already but still he heard the slight hiss when he plunged into the tight ass. 

"Sam," Dean breathed out. "Sammy, it's too much..." 

"Just wait a bit," Sam told his brother. "It'll feel good soon. Relax and I'll show you how amazing it is to get fucked."

Curling his fingers slightly, Sam smiled as Dean gasped. Until now his brother had just knelt on the bed, waiting. Sam brushed over his brother's prostate again and watched in delight that Dean started to fuck himself on Sam's fingers. Slowly at first, still a bit hesitating as if the surge of pleasure had been just a fluke but after a few attempts Dean's shy behavior melted away. 

Moving back and forth, Dean presented his ass to Sam, trying to get the fingers deeper that brought him such delicious pleasure. 

Hair was pushed out of his face when Sam asked, "Are you ready, Dean?" 

Who waited for a few moments to gather some clear thoughts. Yet Sam withdrew his fingers and Dean began to rock backwards, feeling the loss of the warmth he experienced earlier. He missed it and Sam was so close, hovering behind him. That his brother's cock rubbed over his ass still made him a little uncomfortable. To imagine what it must look like, he an older man kneeling on a cheap bed while his well build, yet younger brother had positioned himself behind him. It would be so easy for Sam to push forwards and put his dick in his ass. 

Dean wondered what would feel like. 

"Yes, Sam," he finally said. Dean thought he sounded strong but in truth his words were barely a whisper. 

Sam who was far more self-confident assured his brother, "It's okay, Dean. I promise it will feel good. I'm going to make it you for you." 

"I ... I trust you, Sam." 

It was more difficult than he thought to admit this. Dean had to turn around and look Sam in the eyes. He was greeted by a smile and the two hands on his hips gripped him tighter. Dean trembled a little when he spotted Sam's erect cock. In the next moment he felt it poke against his entrance. A shocked noise escaped his mouth as the feeling of flesh, wet from lube yet much harder and bigger than the fingers, breached his rim. 

Breathing hard, Dean's arms buckled under the weight of the feeling of having Sam inside him. Down there he seemed to be incredible sensitive to touch. Each inch Sam slid deeper, more skin rubbed against his insides.

"You're doing great," Sam praised as Dean squirmed under him. "I was afraid you would be too tight but you're enjoying this, aren't you?"

"Nngh," Dean moaned wordless, helpless as Sam reached around to grab his cock, large and wetting the sheets. 

He didn't resist when Sam placed one hand on his shoulder and pushed him down. His little brother mumbled nonsense, words of praise he could quite understand because the sensation of Sam cock drowned everything out as he began to move. Dean's chest was heaving when Sam started to fuck into him. Slow and insistent, drawing moans from his mouths until Dean laid there helplessly pleading. 

"Oh God, Sam ... it's so big," Dean gasped quietly. Another blush crept over his face as he said the words, admitting how much this turned him on. He would let Sam to everything to him, just to have the feeling of his little brother's cock sliding into him. 

"You're doing good, Dean." Sam worked his way deeper, hanging on his control despite the fact that Dean's hole clenched around him with eagerness while his brother waited for his commands. "Do you enjoy it?" 

As much as Sam wanted to truly start fucking his brother, he can't unless all doubts are removed. He couldn't bear the thought of hurting him. 

"Yes, it's good. It's so good, Sam. Please..." Dean hissed, now more desperate than before. He's writhing, moving his hips to get more friction. Long Sam's cock has stopped burning. Now Dean just wants. Wanted to have more of Sam who's hands gripping his hips tight enough to leave bruises. Dean can't even deny that he liked the way Sam is pressing him down, allowing him not to move at all. It created a feeling of security, knowing that Sam was there. 

"Please what, Dean?" Sam asked. 

Just as Dean opened his mouth, Sam began to move. 

"Oh please," Dean whispered and his hips bucked, his movements growing erratic as the feeling of Sam filling him out only increased. "Please, Sammy. Please ... more."

Sam murmured words of praise as Dean sobbed his encouraging cries into the pillow.


End file.
